Issue 66, 2023
From the journal:

Chemical Communications

Hydroxamate-directed access to β-Kdo glycosides†

Sourav Pramanik,a   Soumik Mondal,‡a   Alexander Chinarev, ORCID logo b   Nicolai V. Bovinb  and  Jaideep Saha ORCID logo §*c  

* Corresponding authors

a Department of Biological and Synthetic Chemistry, Centre of Biomedical Research (CBMR), Lucknow 226014, India

b Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia

c Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali 160062, India
E-mail: jdsaha2000@gmail.com, jsaha@niper.ac.in

Abstract

The reaction repertoire for forming transient aziridinone or azaoxyallyl cations from α-halohydroxamate is conceptually extended to design Kdo-glycosyl donors by installing the hydroxamate moiety at an anomeric centre, which is shown to be highly effective for stereoselective access to β-Kdo glycosides. The pivotal roles of hydroxamate over amide are revealed in control experiments.

Graphical abstract: Hydroxamate-directed access to β-Kdo glycosides

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Article information

DOI
https://doi.org/10.1039/D3CC02609D
Article type
Communication
Submitted
30 May 2023
Accepted
23 Jul 2023
First published
24 Jul 2023

Chem. Commun., 2023,59, 10028-10031

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Hydroxamate-directed access to β-Kdo glycosides

S. Pramanik, S. Mondal, A. Chinarev, N. V. Bovin and J. Saha, Chem. Commun., 2023, 59, 10028 DOI: 10.1039/D3CC02609D

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